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Genipin derivatives and their preparation method and use

A technology of genipin and derivatives, which is applied in the field of novel genipin derivatives, and can solve the problem that the inhibitory activity of PTP1B protein is not obvious

Active Publication Date: 2017-11-24
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the inhibitory activity of existing genipin and its derivatives on PTP1B protein is not obvious

Method used

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  • Genipin derivatives and their preparation method and use
  • Genipin derivatives and their preparation method and use
  • Genipin derivatives and their preparation method and use

Examples

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preparation example Construction

[0084] Preparation of genipin derivatives

[0085] The present invention also provides a method for preparing the above-mentioned compound of formula I, said method comprising the steps of:

[0086] In a preferred embodiment, the method for the genipin derivative shown in the formula (A) may further comprise the steps:

[0087] (1) Take genipin and add it to a certain volume of R 2 -OH, stirring at a certain temperature, and adding a few drops of concentrated hydrochloric acid to catalyze the compound shown in formula (II)

[0088] In another preferred example, the temperature is preferably 60-100°C.

[0089] (2) get 1 molar equivalent of the compound shown in formula (II) 2 molar equivalents of triethylamine and dichloromethane are added to a round bottom flask, under an ice-water bath, 1.5 molar equivalents of chlorination reagent are added, a certain amount of 4-dimethylaminopyridine (DMAP) is catalyzed, and the reaction is carried out at room temperature to obtain C...

Embodiment 1

[0125] Synthesis of 1-methoxygenipin

[0126] The specific steps of this example include: dissolving genipin (10 g, 44 mmol) in methanol (70 ml), adding two drops of concentrated hydrochloric acid to the solution for catalysis, and heating to reflux for 7 hours. After the reaction, concentrate under reduced pressure, add a few drops of 1N sodium hydroxide solution to adjust the pH to neutral, extract three times with ethyl acetate, combine the organic phases, wash the organic phases with saturated brine three times, and dry the organic phases with anhydrous sodium sulfate . Concentration under reduced pressure gave brown oily liquid 1-methoxygenipin (10.620 g, 44 mmol) with a yield of 98%. 1 HNMR (400MHz, CDCl 3 ): δ7.41-7.54(m,1H),5.75-5.88(m,1H),4.46(d,J=8.2Hz,1H),4.12-4.28(m,2H),3.64-3.75(m,3H ),3.40-3.54(m,3H),3.13-3.23(m,1H),2.86(dd,J=8.5,16.5Hz,1H),2.59(t,J=7.6Hz,1H),2.06(dd, J=9.0,16.4Hz,1H).

Embodiment 2

[0128] Synthesis of 1-methoxy-2-(chloromethyl)genipin

[0129] The specific steps of this example include: dissolving 1-methoxygenipin (10.620g, 44mmol) and triethylamine (8.905g, 88mmol) in dichloromethane (70ml), slowly adding benzenesulfonyl chloride dropwise in an ice-water bath (11.656g, 66mmol), after the dropwise addition was completed, DMAP (200mg) was added to catalyze the reaction at room temperature for 40 hours. After the reaction was completed, 1N sodium hydroxide solution (10 ml) was added for extraction three times, and the organic phases were combined. 1N hydrochloric acid solution was added to the organic phase to adjust the pH to neutral, the extracted organic phase was washed three times with saturated brine, and the organic phase was dried over anhydrous sodium sulfate. After concentration under reduced pressure, purification by silica gel column chromatography (petroleum ether: ethyl acetate = 15:1) gave 1-methoxy-2-(chloromethyl)genipin (5.603g, 22mmol) ...

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Abstract

The invention provides genipin derivatives and their preparation method and use and specifically discloses genipin derivatives having novel structures shown in the formula I. The groups are defined in the specification. The invention also discloses a preparation method of the compounds and use of the compounds as protein tyrosine phosphatase 1B (PTP1B) inhibitors. The compounds produce good anti-diabetic effects and have an application value in preparation of drugs for treating type II diabetes.

Description

technical field [0001] The present invention relates to the field of medicine, in particular, the present invention relates to a novel genipin derivative, its preparation method and application. Background technique [0002] With the improvement of people's living standards, the number of patients with diabetes and obesity continues to increase. The pathogenesis of diabetes is complex, generally due to the interaction of genetic and environmental factors. Diabetes can be divided into type I and type II according to the cause of the disease, and type II diabetes accounts for about 95% of the total number of diabetic patients. Insulin resistance is a hallmark of type 2 diabetes. In recent years, many molecular targets mainly present in peripheral tissues have been widely used to study the increase of insulin-mediated signaling. PTP1B, which negatively regulates insulin signaling, has been extensively studied as a potential target for the treatment of diabetes and obesity. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/94C07H17/04C07H1/00A61K31/352A61K31/7048A61P3/10A61P3/04
CPCC07D311/94C07H1/00C07H17/04
Inventor 傅磊亓云月杨凤志姜发琴谢东升邓欣贤王君韬孙冉郭秋圆张秋晨
Owner SHANGHAI JIAO TONG UNIV
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